Heidi Klum is casual cool and an oversize sweater shirt and jogger set. Her all black outfit is one that never goes out of style and made for a comfy errand run! Nasty Gal has a relaxed set including both pieces for $27 that resembles Heidi‘s.

Nicky Hilton's unique twist on a traditional trench coat is exactly what we need to spice up our winter outerwear! Her deconstructed plaid trench coat by Monse retails for $$$—but our find has a similar feel with the same avant garde look.

Olivia Palermo continues to give us winter style inspiration with upgraded neutrals and classic pieces. Her traditional peacoat is refreshed in a bold rust orange hue. We love how she uses unexpected pops of color in her outfits like she does here.

Teen Wolf actress Holland Roden wears the cutest casual look while out and about. Her bold abstract print pants steal the show and work as a perfect base for simple staples like a white v-neck tee. We love the relaxed look and feel of this fan favorite from Old Navy!

Olivia Palermo is known for blending classic and trendy pieces in the most chic way—and this look shows us exactly how it’s done! Her monochrome sweater/skirt is a winning combination in a beautiful blue color and gorgeous mix of textures. The relaxed knit turtleneck balances the feminine frill of her pleated tulle midi skirt by Max&Co.